Jun 26, 2026 9:50 PM
Updated Jun 26, 2026 10:18 PM

Trailing the division-leading Brewers, Chicago enters a high-stakes gauntlet against NL Central rivals and Wild Card contenders. The surging offense must overcome elite pitching to secure a postseason foothold.

The Chicago Cubs have a very important stretch coming up before the All-Star break. 

That important stretch begins on Friday night against the Milwaukee Brewers. The Cubs will begin a three-game series on the road against the team they are trailing in the National League Central division standings. They currently sit 6 ½ games behind the Brewers for first place. 

This is no doubt going to be a tough series. The Brewers are throwing out their three best pitchers (Jacob Misiorowski, Kyle Harrison, and Brandon Woodruff), and the Cubs will be rolling with Colin Rea on Friday, David Peterson on Saturday, and either Vince Velasquez or Jordan Wicks on Sunday. 

The North Siders can’t afford to get swept in this series after already getting swept by the Brewers in mid-May. Another Brewers sweep would push Chicago back to 9 ½ games in the division. 

After three tough games against the Brewers, the Cubs will face two teams that are right alongside them in the Wild Card race. They will host both the San Diego Padres and St. Louis Cardinals for a three-game series at Wrigley Field. 

The Cubs currently own the second Wild Card spot with a 44-37 record. But the Cardinals are right behind them with a 42-36 record, and the Padres are only one game back with a 42-37 record. These six games could help Chicago gain some separation in the Wild Card standings heading into the All-Star break. 

The Cubs will then end the “first-half” of the season on the road with two series against the Baltimore Orioles and Cincinnati Reds. The Orioles are 10-12 this month, while the Reds are 7-14 so far in the month of June. 

It is important for the North Siders to finish the first half on a strong note. They have played better baseball as of late and are coming off a four-game sweep over the New York Mets. The Cubs have won 10 of their last 13 games. 

The offense deserves a ton of credit for this recent winning streak, as the team is averaging 7 runs per game since June 11. Players like Pete Crow-Armstrong and Dansby Swanson have certainly stepped up during this 13-game stretch. 

But the whole offense will need to be at its best on Friday against the NL Cy Young front-runner. 

Misiorowski currently owns a 1.45 ERA and a 39.1% strikeout rate across 93 innings pitched this season. In his one start against the Cubs this year, the Brewers right-hander threw six shutout innings with eight strikeouts. 

Friday’s matchup against Misiorowski is the start of a vital stretch for Chicago. 

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